Reaktion #42379

Reaktionsgleichung

lithium borohydride

hydrochloric acid

3-bromo-5-(methoxycarbonyl)benzoic acid

ethanol

→

title compound

3-Bromo-5-(hydroxymethyl)benzoic acid

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe reaction is stirred 1.5 h
2. 2
   workup.ADDITIONis added until gas evolution
3. 3
   ExtraktionThe aqueous layer is extracted with chloroform
4. 4
   Waschenthe organic layer is washed with brine
5. 5
   Trocknendried (magnesium sulfate)
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated under reduced pressure

Vorschrift

To an ice-cold solution of 3-bromo-5-(methoxycarbonyl)benzoic acid prepared by the method in Preparation 2 (10.3 g, 40 mmol) in anhydrous tetrahydrofuran (100 mL) is added lithium borohydride (12 g, 550 mmol) portion-wise. The reaction is stirred 4 h at this temperature. Absolute ethanol (20 mL) is added dropwise, and the reaction is stirred 1.5 h. The reaction is slowly poured on ice, and 10% hydrochloric acid (aq) is added until gas evolution ceased. The aqueous layer is extracted with chloroform, and the organic layer is washed with brine, dried (magnesium sulfate), filtered, and concentrated under reduced pressure to give the title compound. ESI MS m/z 229, 231 [M−H]−.

Quelle